Process of producing aminoacetylpyrocatechin.



UNITED STATES PATENT OFFICE.

WILHELM GRUETTEFIEN, F VOHWINKEL, NEAR ELBERFELD, GERMANY, ASSIGNOR TOFABBENFABRIKEN VORM. FRIEDR. BAYER & CO., OF ELBERFELD, GERMANY, A

CORPORATION OF GERMANY.

PROGESS PRODUCING AMINOAGETYLPYBOCATEGHIN.

Specification of Letters Patent. Patented Sept, 13, 1910,

i No Drawing; Original application filed March 9, 1909, Serial No.482,392. Divided and this application filed Jul 22, 1909.Serie1No.50B,986. a

To all whom it may comcrn:

Be it known that I, WILHELM GRUE'ITE- 1mm doctor of philosophy, chemist,citizen of the German Em ire, residing at Vohwinkel, near Elberfe dGermany, have invented new and useful improvements in New Processes ofProducin Aminoacetylpyrocatechin, of which the ollowing is aspecification. I v

This application which, is a divisional a plication of my applicationSerial 0. 482,392 dated March 9, 1909 relates to a new and valuableprocess for producing the known aminoacet lpyrocatechim I have found tat ethers of n-phthaliminoacetylpyrocatechins having the formula:

OR I

(R mean'in alkiyl) can be obtained by treating dialky etlers ofyrocatechin with phthalylglyc l chlorid see Bem'chte der Deutsclum 0'molten Gesellschaft 40, page 2649) in the presence of aluminum chlorid.The new compounds thus obtained yield by saponification the knownaminoacetylpyrocatechin:

' renal glands.

which has the valuable therapeutic property of increasing theblood-pressure'in the same way as the substance contained in the supra-My discove affords a new and very useful way of pro ucing this valuablecompound which is. employed in doses of 1/50 m dissolved in water, forsubcutaneous lIlJBCtiOHS.

/COOH coon H01 Phthalic acid. Aminoacetyl ocatechin hydroc orid.

Example: 40 parts b weight of finely powdered aluminum chl orid areadded to a mixture of 40 parts of phthalylglycyl chlorid and 40 parts byweight of veratrol (dimethvl ether of pyrocatechin). It is heated. forhalf an hour on the water bath until the evolution of HCl ceases. Themelt is carefully mixed with ice and 50 parts by Wei ht of hydrochloricacid contaming 20% Cl, warmed on the water-bath and unchanged veratrolis removed by distillation with steam and the residue is then ex- Theabove regti g ly @1826; v u

'' actionis diluted tars are removed filtration, the filtmte is er andfrom the acid watery soiufien 1:119 aminoacetopyrocateehinis-frecipitated by ,the addition of ammonia.

, gw q 2. TheProcess for pmdmillg Q at a 4 v i v dniutin n act pads by 2ii ph war are him 5511i; ofi d i I e00 a proximal: o the rewi 51 water,insoluble matactlom After extmcted IL Thecgrmocss for pmdncingaminoacetylwhich rtofiess cgnsists in fir st rem: 1113011 1 e ers o pteehm with j thalylglycy chlorid in t e presence of aluminum cifloridand then sapo flie pmdncts thus produced, sutially as desm-ibed.

as, Hz.

I v phthalic acid are the re- 3211f Wm" h m -P thaly flglycywhlonduminnli ;nhloridland than $11 0 with acids, n"

or p ueing gminoaoatylctmg i a z fi in first Tea, upwYeraQWi'Y 1 1claim-id in the presence of aln inum l z l r i and than sapo the productthus produced-with acids, an isolating the :fi-ee base by maans ofsubstantially as de- 4. e pyroqmtec scribed.

In testi iiol whereof I have hereuzito set my hand m e presence of twoWZltIIGSSBS.

V Witnesses:

OTTO .Kiimu, WILLY Kim.

catechin a pr me 7

